Water → HCID 68486454, compound

HRID 1878006Notes

Reaction equation

HRID 1878006 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH2:18])([C:13]([F:16])([F:15])[F:14])[C:7]=2[CH:19]=1.C(N(CC)CC)C.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH:18][S:34]([C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)(=[O:36])=[O:35])([C:13]([F:15])([F:16])[F:14])[C:7]=2[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 68487391HCID 68487391, compound

Product 1

HCID 68486454HCID 68486454, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

While stirring a solution of [6-chloro-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methylamine hydrochloride (60 mg, 0.19 mmol) in THF (1 mL) at room temperature, triethylamine (66 μL, 0.47 mmol) and 4-fluorobenzenesulfonyl chloride (44 mg, 0.23 mmol) were sequentially added thereto. After the reaction solution was stirred overnight at room temperature, water was added thereto. Then, the resulting solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (58 mg, 70%) was obtained as a white solid.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the drying agent was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (58 mg, 70%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-2fa2326f33b943b7a15e293f81440f73
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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